| 1 | Sat 12 Aug | 3 0-1 v LewesLewes 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Wed 16 Aug | 31-3 v HorshamCray Wanderers 1-3 Horsham | Isthmian League - Premier Division |
| 3 | Sat 19 Aug | 30-1 v Billericay TownCray Wanderers 0-1 Billericay Town | Isthmian League - Premier Division |
| 4 | Sat 26 Aug | 30-2 v Enfield TownEnfield Town 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Mon 28 Aug | 30-3 v Hastings UnitedHastings United 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 6 | Sat 2 Sep | 35-1 v NewhavenCray Wanderers 5-1 Newhaven | Emirates FA Cup First Qualifying Round |
| 7 | Wed 20 Sep | 32-3 v RamsgateRamsgate 3-2 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 8 | Sat 23 Sep | 32-1 v CheshuntCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
| 9 | Tue 26 Sep | 3 3-2 v Phoenix SportsPhoenix Sports 2-3 Cray Wanderers | Kent Senior Cup First Round |
| 10 | Sat 30 Sep | 30-3 v KingstonianKingstonian 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 11 | Tue 3 Oct | 63-0 v Concord RangersConcord Rangers 0-3 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Sat 7 Oct | 3 1-0 v Needham MarketNeedham Market 0-1 Cray Wanderers | Isuzu FA Trophy Third Qualifying Round |
| 13 | Sun 15 Oct | 3 1-4 v HornchurchCray Wanderers 1-4 Hornchurch | Isthmian League - Premier Division |
| 14 | Sat 21 Oct | 31-1 v Potters Bar TownPotters Bar Town 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 15 | Tue 24 Oct | 31-2 v Canvey IslandCanvey Island 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Sat 28 Oct | 33-3 v Chesham UnitedCray Wanderers 3-3 Chesham United | Isuzu FA Trophy First Round |
| 17 | Tue 31 Oct | 30-5 v Ebbsfleet UnitedEbbsfleet United 5-0 Cray Wanderers | Kent Senior Cup Second Round |
| 18 | Sat 4 Nov | 3 3-1 v Wingate & FinchleyWingate & Finchley 1-3 Cray Wanderers | Isthmian League - Premier Division |
| 19 | Wed 8 Nov | 34-2 v Tooting & Mitcham UnitedCray Wanderers 4-2 Tooting & Mitcham United | London County Cup First Round |
| 20 | Sat 11 Nov | 31-0 v Carshalton AthleticCray Wanderers 1-0 Carshalton Athletic | Isthmian League - Premier Division |
| 21 | Sat 18 Nov | 31-4 v Weston-super-MareWeston-super-Mare 4-1 Cray Wanderers | Isuzu FA Trophy Second Round |
| 22 | Sat 25 Nov | 31-1 v Dulwich HamletCray Wanderers 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 23 | Wed 29 Nov | 32-2 v WhitehawkCray Wanderers 2-2 Whitehawk | Isthmian League - Premier Division |
| 24 | Sun 10 Dec | 33-3 v Haringey BoroughCray Wanderers 3-3 Haringey Borough | Isthmian League - Premier Division |
| 25 | Sat 16 Dec | 30-1 v Hashtag UnitedHashtag United 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 26 | Tue 26 Dec | 30-0 v MargateCray Wanderers 0-0 Margate | Isthmian League - Premier Division |
| 27 | Fri 29 Dec | 32-0 v Enfield TownCray Wanderers 2-0 Enfield Town | Isthmian League - Premier Division |
| 28 | Mon 1 Jan | 30-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 29 | Sat 6 Jan | 3 1-1 v LewesCray Wanderers 1-1 Lewes | Isthmian League - Premier Division |
| 30 | Tue 9 Jan | 31-2 v Bognor Regis TownBognor Regis Town 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 31 | Wed 24 Jan | 33-0 v FisherCray Wanderers 3-0 Fisher | London County Cup Second Round |
| 32 | Sat 10 Feb | 32-1 v MargateChatham Town 2-1 Margate | Isthmian League - Premier Division |
| 33 | Tue 13 Feb | 31-1 v Billericay TownBillericay Town 1-1 Chatham Town | Velocity Cup Quarter Final |
| 34 | Sat 17 Feb | 33-0 v LewesLewes 0-3 Chatham Town | Isthmian League - Premier Division |
| 35 | Sat 24 Feb | 36-3 v Billericay TownChatham Town 6-3 Billericay Town | Isthmian League - Premier Division |
| 36 | Sat 2 Mar | 30-2 v Carshalton AthleticCarshalton Athletic 2-0 Chatham Town | Isthmian League - Premier Division |
| 37 | Sat 9 Mar | 32-1 v Concord RangersChatham Town 2-1 Concord Rangers | Isthmian League - Premier Division |
| 38 | Tue 12 Mar | 34-2 v Ashford UnitedChatham Town 4-2 Ashford United | Velocity Cup Semi Final |
| 39 | Sat 16 Mar | 31-1 v Hastings UnitedHastings United 1-1 Chatham Town | Isthmian League - Premier Division |
| 40 | Sat 23 Mar | 32-1 v Haringey BoroughChatham Town 2-1 Haringey Borough | Isthmian League - Premier Division |
| 41 | Fri 29 Mar | 32-2 v Cray WanderersCray Wanderers 2-2 Chatham Town | Isthmian League - Premier Division |
| 42 | Mon 1 Apr | 34-1 v KingstonianChatham Town 4-1 Kingstonian | Isthmian League - Premier Division |
| 43 | Sat 6 Apr | 31-2 v HornchurchHornchurch 2-1 Chatham Town | Isthmian League - Premier Division |
| 44 | Sat 13 Apr | 32-0 v Folkestone InvictaChatham Town 2-0 Folkestone Invicta | Isthmian League - Premier Division |
| 45 | Sat 20 Apr | 31-3 v HorshamChatham Town 1-3 Horsham | Isthmian League - Premier Division |
| 46 | Wed 1 May | 31-1 v HorshamChatham Town 1-1 Horsham | Isthmian League - Premier Division Play-off Semi Final |
| 47 | Mon 6 May | 30-3 v Enfield TownChatham Town 0-3 Enfield Town | Isthmian League - Premier Division Play-off Final |
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